WO2010026230A1 - Composition retardatrice de flamme renfermant un dérivé de l'acide phosphonique - Google Patents

Composition retardatrice de flamme renfermant un dérivé de l'acide phosphonique Download PDF

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Publication number
WO2010026230A1
WO2010026230A1 PCT/EP2009/061489 EP2009061489W WO2010026230A1 WO 2010026230 A1 WO2010026230 A1 WO 2010026230A1 EP 2009061489 W EP2009061489 W EP 2009061489W WO 2010026230 A1 WO2010026230 A1 WO 2010026230A1
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Prior art keywords
triazine
tert
bis
flame
butyl
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PCT/EP2009/061489
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German (de)
English (en)
Inventor
Volker Butz
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Thor Gmbh
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Priority to DK09782635.8T priority Critical patent/DK2331625T3/da
Priority to AT09782635T priority patent/ATE541889T1/de
Priority to US12/737,924 priority patent/US8349925B2/en
Priority to EP09782635A priority patent/EP2331625B1/fr
Publication of WO2010026230A1 publication Critical patent/WO2010026230A1/fr
Priority to US13/705,058 priority patent/US8853307B2/en

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • C08K5/5353—Esters of phosphonic acids containing also nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
    • C08K5/3477—Six-membered rings
    • C08K5/3492—Triazines
    • C08K5/34926—Triazines also containing heterocyclic groups other than triazine groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/35—Heterocyclic compounds having nitrogen in the ring having also oxygen in the ring
    • C08K5/357—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/527—Cyclic esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
    • C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
    • C08K5/5333—Esters of phosphonic acids
    • C08K5/5357—Esters of phosphonic acids cyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K2201/00—Specific properties of additives
    • C08K2201/014—Additives containing two or more different additives of the same subgroup in C08K

Definitions

  • the present invention relates to a flame retardant composition containing a synergistic flame retardant mixture and a method of flame retardation of a polymer substrate by adding this flame retardant composition. Furthermore, the invention relates to polymers containing this flame retardant composition.
  • Polymers are now often rendered flame retardant by adding these to phosphorus or halogen containing compounds or mixtures thereof. Also, mixtures of phosphorus and nitrogen containing compounds are currently often used as flame retardants. An associated problem is usually a too weak flame protection effect or too low thermal stability of the resulting finished plastic.
  • salts of phosphinic acids have proven to be effective flame retardant additives for polymers, in which case both alkali metal salts (DE-A 2 252 258) and salts of other metals (DE-A 2 447 727) are used. These flame-retardant additives lead to a small change in the thermal properties of the plastic, but still have too low a flame retardant effect.
  • the market for flame retardants currently includes products that act to disrupt any combustion process by chemical and / or physical processes. It has been shown that these agents act during the combustion of an article in either the gas phase, the condensed phase or in both phases. It is believed that, for example, organic haloforms (such as decabromodiphenyl oxide, hexabromocyclodecane (HBCD), tetrabromobisphenol A) will produce hydrogen halide (HX) which in the gas phase interacts with free radical organic "fuel” from the polymer substrate. Synergists for reaction with HX have been proposed to form additional chemical species that interfere with gas phase combustion, such as a reaction of antimony oxide with HX to generate antimony halide and hydrogen.
  • organic haloforms such as decabromodiphenyl oxide, hexabromocyclodecane (HBCD), tetrabromobisphenol A
  • Antimony compounds such as antimony trioxide also act as radical scavengers in combination with halogen compounds. Thus, the spread of the fire can be inhibited.
  • antimony and the typical halogen compounds are efficient in terms of cost performance, there has recently been a great deal of concern due to the toxicity of the by-products formed during combustion in the presence of a halogenated flame retardant.
  • Antimony oxides also often contain trace amounts of arsenic compounds suspected of being carcinogenic. Because of these drawbacks of these compounds, there are currently efforts to replace antimony trioxide and bromine compounds in current commercial flame retardant applications. However, it is very difficult to provide a replacement flame retardant which is not only environmentally friendly but also highly effective.
  • the fillers used include calcium carbonate, magnesium carbonate, zinc borate, silicates, silicones, glass fibers, glass beads, asbestos, kaolin, barium sulfate, calcium sulfate, metal oxides, hydrides and hydroxides such as zinc oxide, magnesium hydroxide, alumina trihydrate, silica, calcium silicate and magnesium silicates.
  • hindered amines long known as light and / or thermal stabilizers for a variety of organic materials susceptible to degradation induced by oxygen, heat and actinic light, have also been recently discussed as flame retardants.
  • NR-hindered amines N-hydrocarbon oxy-substituted hindered amines
  • DE-T 69826477 discusses such NR-hindered amines which are said to have not only UV-stabilizing but also flame-retardant properties.
  • the object underlying the invention is to provide a further highly effective and thermally stable flame retardant composition.
  • the components of the inventive flame retardant composition and should not adversely affect even at high temperatures in the range of about 250 to 300 0 C, the thermal processability of a flame retardant equipped plastic. Further, the components of these flame retardant compositions should synergistically interact and therefore be used in concurrent use at lower concentrations compared to the necessary concentrations in the case of the individual components. Furthermore, the flame retardant composition according to the invention should be free of organic halogen compounds and heavy metals, thereby avoiding the exposure of toxic substances.
  • (A) is a compound or a mixture of 2 or more compounds of
  • a 1 and A 2 independently of one another represent a substituted or unsubstituted, straight-chain or branched alkyl group having 1 to 4 carbon atoms, substituted or unsubstituted benzyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, b) one or more phosphonate compounds ( en) of the formula
  • a 3 and A 4 are independently methyl or ethyl and A 5 is a straight-chain or branched alkyl group having 1 to 4 carbon atoms or a phenyl or benzyl group, each of which may have up to 3 methyl groups, and
  • alkyl or aryl-phosphonic acids wherein alkyl represents a straight-chain or branched alkyl group having 1 to 4 carbon atoms, and aryl is a substituted or unsubstituted benzyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, and a salt or Esters of the aforementioned phosphonic acid, and
  • Ri and R 2 represent the s-triazine unit E, and one of R 3 and R 4 represents the s-triazine unit E, the other of R 3 and R 4 being hydrogen,
  • R represents methyl, cyclohexyl or octyl
  • R 5 is alkyl of 1 to 12 carbon atoms, wherein in the compound of formula II or IIA, when R is cyclohexyl or octyl,
  • T and Ti each represent a tetraamine substituted with Ri-R 4 as defined for formula I, wherein
  • one of the s-triazine units E in each tetraamine is replaced by the group Ei which forms a break between two tetraamines T and Ti, or
  • the group Ei may have both ends in the same tetraamine T, as in formula IIA, in which two of the E residues of the tetraamine are replaced by an Ei group, or
  • all three s-triazine substituents of the tetraamine T Ei may mean so that a residue Ei makes the connection between T and Ti and the second residue Ei has both ends in the tetraamine T, and
  • the mixture may itself already be a flame retardant composition or form a flame retardant composition in combination with further constituents mentioned below.
  • component (B) may be one or more 1,3,5-triazine compound (s) selected from tris-2-hydroxyethyl isocyanurate, melamine, melamine cyanurate, melamine phosphate, poly (2,4-) (piperazin-1, 4-yl) -6- (morpholin-4-yl) -1,3,5-triazine], Dirne has laminophosp,
  • the components of the mixture may be selected from a few, 2 or 3 compounds of group (a), (b) and (c), and wherein the symbols have the following meaning:
  • Ei, E 2 , E 3 and E 4 independently represent straight-chain or branched alkyl having 1 to 4 carbon atoms or Ei and E 2 independently represent alkyl having 1 to 4 carbon atoms and E 3 and E 4 taken together represent pentamethylene or Ei and E 2 and E 3 and E 4 taken together are pentamethylene,
  • R 1 is straight or branched alkyl of 1 to 18 carbon atoms, cycloalkyl of 5 to 12 carbon atoms, a bicyclic or tricyclic hydrocarbon radical of 7 to 12 carbon atoms, phenylalkyl of 7 to 15 carbon atoms, aryl of 6 to 10 carbon atoms or the aryl is substituted with 1 to 3 alkyl having 1 to 8 carbon atoms
  • R 2 represents hydrogen or a linear or branched chain alkyl having 1 to 12 carbon atoms,
  • R 3 is alkylene having 1 to 8 carbon atoms or -C (O) -, -C (O) -R 4 -, -C (O) NR 2 - or - C (O) -NR 2 -R 4 ,
  • R 4 represents alkylene of 1 to 8 carbon atoms
  • R5 is hydrogen, a linear or branched chain alkyl having 1 to 12 carbon atoms or
  • R 6 is alkylene having 2 to 8 carbon atoms or R 6
  • A represents -O- or -NR 7 -, wherein R 7 represents hydrogen, a straight or branched chain alkyl having 1 to 12 carbon atoms, or R 7
  • T is phenoxy, phenoxy substituted with one or two alkyl groups of 1 to 4 carbon atoms, alkoxy of 1 to 8 carbon atoms or -N (R 2 ) 2 , with the condition that R 2 is not hydrogen, or T
  • X is -NH 2 , -NCO, -OH, -O-glycidyl or -NHNH 2
  • Y is -OH, -NH 2 , -NHR 2 , wherein R 2 is not hydrogen; or Y -NCO, -
  • R 2 is alkyl or the alkyl interrupted by one to four
  • Oxygen atoms, or R 3 represents -Y-CH 2 -OR 2 ; or wherein the hindered amine compound is a mixture of N, N ', N'"- tris ⁇ 2,4-bis [(1-hydrocarbyloxy-2,2,6,6-tetramethylpiperidin-4-yl) alkylamino] -s-triazine -6-yl ⁇ -3,3'-ethylenediiminodipropylamine;
  • Ri and R 2 represent the s-triazine unit E, and one of R 3 and R 4 represents the s-triazine unit E, the other of R 3 and R 4 being hydrogen,
  • R represents methyl, propyl, cyclohexyl or octyl
  • R 5 is alkyl of 1 to 12 carbon atoms, wherein in the compound of formula II or IIA, when R is propyl, cyclohexyl or octyl,
  • T and Ti each represent a tetraamine substituted with Ri-R 4 as defined for formula I, wherein
  • the group Ei may have both ends in the same tetraamine T as in formula IIA, wherein two of the units E of the tetraamine are replaced by a group E 1 , or
  • all three s-triazine substituents of tetraamine may be T Ei, such that one egg connects T and Ti and the second egg has both ends in tetraamine T;
  • L is propanediyl, cyclohexanediyl or octanediyl; wherein in the compound of formula III
  • G, Gi and G 2 are each tetraamines substituted with Ri-R 4 as defined for formula I, except that G and G 2 each have one of the s-triazine units E replaced by E 1 and Gi two from the triazine units E, replaced by E 1 , so that there is a bridge between G and Gi and a second bridge between Gi and G 2 ; wherein the mixture is prepared by reacting two to four equivalents of 2,4-
  • index n is in the range of 1 to 15;
  • Ri 2 is C 2 -Ci2 alkylene, C4-Ci2 alkenylene, C 5 -C 7 cycloalkylene, C 6 -C 7 cycloalkylene-di (dC 4 - alkylene), C 4 alkylenedi (C 5 -C 7 -cycloalkylene), phenylenedio (Ci-C 4 -alkylene) or C 4 -Ci 2 - alkylene, interrupted by 1, 4-piperazinediyl, -O- or> N-Xi, wherein Xi C 1 - Ci 2 -acyl or (Ci-Ci 2 -alkoxy) carbonyl or has one of the definitions given below for Ri 4 with the exception of hydrogen; or Ri 2 represents a group of the formula (Ib ') or (Ic'); -CH 2 -CH-CH 2 -
  • X 2 is C 1 -C 6 -alkyl, C 3 -C 4 -cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 -alkyl; Phenyl which is unsubstituted or substituted with 1, 2 or 3 Ci-C 4 alkyl or C 1 -C 4 -
  • Alkoxy is substituted, CyCcrPhenylalkyl which is unsubstituted or substituted on the phenyl with 1, 2 or 3 Ci-C 4 alkyl, and the radicals X 3 are independently C 2 -C 2 -alkylene;
  • Cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 -alkyl; C 3 -C 18 -
  • C 1 -C 4 -alkyl is substituted; Tetrahydrofurfuryl or C 2 -C 4 alkyl which is in the 2, 3 or 4
  • Y represents -O-, -CH 2 -, -CH 2 CH 2 - or> N-CH 3 represent; or -N (R M ) (R IS ) additionally represents a group of formula (Ie '); the radicals A independently of one another represent -OR13, -N (Ri4) (Ris) or a group of the formula (HId);
  • X represents -O- or> N-Ri 6 ,
  • R 1 is hydrogen, C 1 -C 18 -alkyl, C 3 -C 18 -alkenyl, C 5 -C 12 -cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4 -alkyl; CyCcrPhenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4 -alkyl; Tetrahydrofurfuryl, a group of formula (Ulf),
  • Alkyl is straight-chain or branched and is, for example, methyl, ethyl, isopropyl, n-propyl, n-butyl, sec-butyl, tert-butyl, n-hexyl, n-octyl, 2-ethylhexyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-hexydecyl or n-octadecyl.
  • Cycloalkyl groups include cyclopentyl and cyclohexyl; typical cycloalkyl groups include cyclohexyl.
  • the one or more phosphonate compound (s) of component (A) is one or more phosphonate compound (s) of the formula wherein A 1 and A 2 independently represent a substituted or unsubstituted straight or branched alkyl group of 1 to 4 carbon atoms, substituted or unsubstituted benzyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl.
  • the alkyl group may be a haloalkyl group substituted with one, two or three halogen atoms selected from chlorine and bromine.
  • a 1 and A 2 may be independently phenylalkyl having 7 to 9 carbon atoms or phenylalkenyl having 8 to 10 carbon atoms, which may be substituted in the alkyl radical.
  • Other phosphonate compounds of the above formula are disclosed in US Patent US 4,174,343 and DE 26 30 693, which are incorporated by reference into the disclosure of the present invention.
  • the phosphonate compound (A) contained in the flame-retardant composition is a compound of the following structural formula
  • a 1 and A 2 are independently alkyl of 1 to 4 carbon atoms, preferably a methyl group, an ethyl group and / or a propyl group, more preferably alkyl of 1 to 2 carbon atoms, and most preferably a methyl group.
  • the phosphonate compound is the dimethyl spiro phosphonate in which the substituents A 1 and A 2 of the formula shown above are methyl groups.
  • the one or more phosphonate compound (s) of component (A) is one or more phosphonate compound (s) of the formula
  • a 3 and A 4 are independently methyl or ethyl and A 5 is a straight-chain or branched alkyl group having 1 to 4 carbon atoms or a phenyl or benzyl group, each of which may have up to 3 methyl groups.
  • the one or more phosphonate compound (s) are compounds of the formula shown below
  • a 3 and A 4 are independently methyl or ethyl and A 5 is a straight-chain or branched alkyl group having 1 to 4 carbon atoms or a phenyl or benzyl group, each of which may have up to 3 methyl groups.
  • a 3 and A 4 are methyl and A 5 is an alkyl group having 1 to 3 carbon atoms.
  • all three substituents A 3 , A 4 and A 5 are methyl.
  • the phosphonate compound present in the mixture or flame retardant composition is an alkylphosphonic acid, more preferably a methanephosphonic acid, ethanephosphonic acid, propanephosphonic acid or a derivative thereof, such as a salt or ester thereof.
  • the salt may be an ammonium salt, guanidinium salt, DCDA, guanylurea, melamine, ethylenediamine or piperazine salt. If the methanephosphonic acid in the form of its ester, this may be an alkyl ester having 1 to 3 carbon atoms.
  • It is preferably a methyl, ethyl, propyl or trimethylolpropane, substituted or unsubstituted aryl, substituted or unsubstituted benzyl, substituted or unsubstituted phenyl esters of alkylphosphonic acid.
  • esters are suitable, such as the 3- (dimethylphosphono) propionic acid methylolamide, available under the brand name Amgard CU from Rhodia Inc., or AFLAMMIT KWB from THOR GmbH, Speyer, the Amgard CT from Rhodia Inc , or AFLAMMIT PE conc from THOR GmbH, Speyer, the Amgard V 490 from Rhodia Inc., the AFLAMMIT TL 1002 from THOR GmbH, Speyer, the Fyrol PMP from Akzo, the FRX 100 from FRX Polymers, the Levagard DMPP from Clariant and the Exolit OP 560 from Clariant.
  • the phosphonate compound contains a phenylphosphonic acid, eg Fyrol PMP, available from AkzoNobel or FRX 100, available from FRX Polymers.
  • the mixture or the flame-retardant composition according to the invention further comprises one or more free-radical initiators.
  • radical generator in the context of the present invention is to be understood as meaning a compound which is capable of releasing a free-radical compound by chemical or physical means.
  • the free-radical compound is preferably a Br, Cl or H radical.
  • Such a radical generator is, for example, a compound which can liberate bromine and / or chlorine and / or hydrogen in the form of the respective free radical.
  • the radical generator is NH 4 Br or NH 4 Cl.
  • the free radical generator may be both an inorganic and an organic compound.
  • the radical generator may be a halogenated flame retardant.
  • the 1,3,5-triazine compounds (B) are used in the form of their hydrobromides or hydrochlorides.
  • the proportion of the radical generator based on the 1,3,5-triazine compound (s) (B) can vary over a wide range.
  • the proportion is generally chosen so that per mole of 1, 3,5-triazine compound from 0.001 to 1000 mol, preferably 0.01 to 100 mol, particularly preferably 0.1 to 10 mol radicals are formed.
  • the 1,3,5-triazine compound (B) contained in the flame retardant composition is melamine, according to a preferred embodiment of the invention in combination with a free radical generator.
  • the 1,3,5-triazine compound, ie the melamine is in the form of the hydrobromide or hydrochloride.
  • the 1,3,5-triazine compound (B) contained in the flame retardant composition is melamine cyanurate, in accordance with a preferred embodiment of the invention in combination with a free radical generator.
  • the 1,3,5-triazine compound (B) contained in the flame-retarding composition is melamine phosphate, according to a preferred embodiment of the invention in combination with a free-radical generator.
  • the 1,3,5-triazine compound (B) contained in the flame retardant composition is dimelamine phosphate, according to a preferred embodiment of the invention in combination with a free radical generator.
  • the 1,3,5-triazine compound (B) contained in the flame retardant composition is melamine pyrophosphate and / or melamine polyphosphate, according to a preferred embodiment of the invention in combination with a free radical generator.
  • the 1,3,5-triazine compound (B) contained in the flame-retardant composition is poly- [2,4- (piperazin-1,4-yl) -6- (morpholin-4-yl) - 1,3,5-triazine], known under the brand name ppm-Triazine TM, available from Evonik Industries.
  • the poly [2,4- (piperazin-l, 4-yl) -6- (morpholin-4-yl) -l, 3,5-triazine] is used in combination with a radical generator.
  • the 1,3,5-triazine compound (B) contained in the flame retardant composition is tris-2-hydroxyethyl isocyanurate, known under the trade name THEIC TM, available from BASF SE.
  • Compositions containing tris-2-hydroxyethyl isocyanurate and one or more compounds of group Aa) and / or Ab) are further characterized by their usability as hot melt adhesive.
  • the 1,3,5-triazine compound (B) contained in the flame-retardant composition is a hindered amine compound of the above-defined formula I, II, III, IV, V, VI, VII, VIII, IX X or XL
  • the 1,3,5-triazine compound (B) contained in the flame retardant composition is a compound sold under the trade names Budit 310, Budit 311, Budit 312, Budit 314, Budit 3141 from Budenheim KG, Germany or PPM triazine from Evonik Industries, Germany.
  • the abovementioned compounds can be used according to a preferred embodiment of the invention in combination with a free-radical generator.
  • the 1,3,5-triazine compound (B) contained in the flame retardant composition is a hindered amine compound marketed under the trade name FLAMESTAB NOR 116 by Ciba.
  • FLAMESTAB NOR 116 This flame retardant is disclosed in EP 0 889 085, the disclosure of which is incorporated herein by reference.
  • the Flamestab NOR is one or more compounds selected from the group
  • Ri and R 2 represent the s-triazine unit E, and one of R 3 and R 4 represents the s-triazine unit E, the other of R 3 and R 4 being hydrogen,
  • R represents cyclohexyl
  • R 5 is alkyl of 1 to 12 carbon atoms, wherein in the compound of formula II or IIA, when R is cyclohexyl,
  • T and Ti each represent a tetraamine substituted with Ri-R 4 as defined for formula I, wherein
  • the above-described hindered amine compounds according to the formulas I, II, IIA and III may further comprise a mixture of N, N ', N' "- tris ⁇ 2,4-bis [(1-hydrocarbyloxy-2,2,6,6 tetramethylpiperidin-4-yl) alkylamino] -s-triazin-6-yl ⁇ -3,3'-ethylenediimino dipropylamine;
  • the combination of the above-defined 1,3,5-triazine compound (s) (Flamestab NOR TM) with the dimethyl spiro-phosphonate (A) provides a synergistic flame retardant composition that exhibits high potency even at low levels.
  • the synergistic effect of the flame retardant composition according to the invention clearly exceeds the usually observed additive effect of the individual components (A) and (B).
  • components (A) and (B) as flame-retardant components, they can be used for the flame-retardant finishing of plastics in substantially smaller amounts, as in additive effect.
  • a flame retardant composition containing the components (A) and (B) in the weight ratios shown below is hereinafter referred to as
  • “Flame-retardant composition according to the invention” can in addition to the components A and B as flame retardant components in the following specified in more detail
  • Weight ratios have one or more other ingredients.
  • the further constituents may have a flame retardant effect, or they may not have a flame retardant effect, that is to say be an additive.
  • the flame-retardant composition according to the invention consists essentially of the components (A) and B as a flame retardant active component, ie, in addition to the components (A) and (B) probably one or more other flame retardant components may be included , but these are present in such an amount in which there is no contribution of the respective to the overall effect of the resulting mixture.
  • the flame-retardant composition of the invention may be composed of components (A) and (B) as the sole flame retardant Components exist.
  • the flame retardant composition of the invention may be composed of components (A) and (B) as the sole flame retardant Components exist.
  • one or more other ingredients are present without a flame retardant effect, such as conventional additives, which are described in more detail below.
  • the ratio (parts by weight) of the compound (s) (A) to the compound (s) (B) is selected so as to synergize the flame retardancy of the two components.
  • the ratio in the composition is, for example, between 1: 100 to 100: 1, preferably in the range from 1:10 to 10: 1, very particularly preferably in the range from 3: 7 to 7: 1.
  • the amount of component (A) and component (B) used also depends on the effectiveness of the particular compound (s) and the particular field of application.
  • composition of the invention may further comprise acid scavengers.
  • Acid scavengers are, for example, hydrotalcites and amorphous butyric aluminum magnesium carbonates such as those described in US 4,427,816 and US 5,234,981.
  • Hydrotalcite is also known as Hycid or DHT4A.
  • the hydrotalcites may be natural or synthetic.
  • the natural hydrotalcite is believed to have a structure of Mg 6 Al 2 (OH) I 8 COs x 4H 2 O.
  • the flame retardant composition of the invention or the polymer containing this flame retardant composition of the present invention may further contain additives.
  • additives are acid scavengers, which are present in the polymer composition, for example, at a level of from 0.1 to 1.0 percent by weight, based on the weight of the polymer composition.
  • the present acid scavengers are present at 0.2 to 0.8 or 0.4 to 0.6 weight percent, based on the weight of the polymer composition.
  • the acid scavengers thereby assist the present composition in color, odor and stability.
  • the polymers or polymer compositions or the flame retardant composition according to the present invention may further contain additional additives.
  • additional additives are selected mainly from the group of heat stabilizers and / or light stabilizers.
  • the thermal stabilization encompasses both the processing and the application (long-term stability). Such additives are known in the art and most of them are commercially available.
  • Suitable additives are, for example: Antioxidants such as alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol, 2,6 -Di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2- ( ⁇ -methylcyclohexyl) -4,6 dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol,
  • Antioxidants such as alkylated monophenols, for example 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethyl
  • 2,6-di-tert-butyl-4-methoxymethylphenol nonylphenols which are linear or branched in the side chains, for example 2,6-di-nonyl-4-methylphenol, 2,4-dimethyl-6- (1 ' - methylundec-1'-yl) pheno 1, 2, 4-dimethyl-6- (1'-methylheptadec-1'-yl) phenol, 2,4-dimethyl-6- (1'-methyltridec-1 '-yl) pheno 1 and mixtures thereof.
  • Alkylthiomethylphenols for example 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-didodecylthiomethyl-4-nonylphenol.
  • Hydroquinones and alkylated hydroquinones for example, 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl-4-octadecyloxyphenol , 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4 hydroxyphenyl stearate, bis- (3,5-di-tert-butyl-4-hydroxyphenyl) adipate.
  • Tocopherols for example ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol, ⁇ -tocopherol and mixtures thereof (vitamin E).
  • Hydroxylated thiodiphenyl ethers for example 2,2'-thiobis (6-tert-butyl-4-methyl-phenol), 2,2'-thio-bis (4-octylphenol), 4,4'-thiobis (6-tert-butyl) butyl-3-methylphenol), 4,4'-thiobis (6-tert-butyl-2-methylphenol).
  • Alkylidene bisphenols for example, 2,2'-methylenebis (6-tert-butyl-4-methylphenol), 2,2'-methylenebis (6-tert-butyl-4-ethylphenol), 2,2'-methylenebis [4 methyl-6- ( ⁇ -methylcyclohexyl) phenol 1), 2,2'-methylenebis (4-methyl-6-cyclohexyl) phenol), 2,2'-methylenebis (6-nonyl-4-) methylphenol), 2,2'-methylenebis (4,6-di-tert-butylphenol), 2,2'-ethylidenebis (4,6-di-tert-butylphenol), 2,2'-ethylidenebis (6) tert-butyl-4-isobutylphenol), 2,2'-methylenebis [6- ( ⁇ -methylbenzyl) -4-nonylphenyl], 2, 2 '-methylenebis [6- ( ⁇ , ⁇ -dimethylbenzyl)
  • O, N and S benzyl compounds for example 3,5,3 ', 5'-tetra-tert-butyl-4,4'-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzylmercaptoacetate, tridecyl 4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate, tris (3,5-di-tert-butyl-4-hydroxybenzyl) amine, bis (4-tert-butyl-3-hydroxy-2,6 -dimethylbenzyl) dithioterephthalate, bis (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzylmercaptoacetate.
  • Hydroxybenzylated malonates for example, dioctadecyl-2,2-bis (3,5-di-tert-butyl-2-hydroxybenzyl) malonate, dioctadecyl-2- (3-tert-butyl-4-hydroxy-5-methylbenzyl) malonate , Didodecylmercaptoethyl 2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl) malonate, bis [4-
  • Aromatic hydroxybenzyl compounds for example, l, 3,5-tris- (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 1,4-bis (3,5-di-tert -butyl-4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) phenol.
  • Triazine compounds for example 2,4-bis (octylmercapto) -6- (3,5-di-tert-butyl-4-hydroxyanilino) -1, 3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmercapto-4,6-bis (3,5-di-tert-butyl-4-hydroxy-phenoxy) - l, 3,5-triazine, 2,4,6-tris- (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,3,3-triazine, 1,3,5-tris (3 , 5-di-tert-butyl) -4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) isocyanurate, 2,4,
  • Benzylphosphonates for example dimethyl 2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl 3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3,5-di-tert-butyl-4- hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphoronate, the calcium salt of the monoethyl ester of 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid.
  • Acylaminophenols for example, 4-hydroxylauranilide, 4-hydroxystearanilide, octyl-N- (3,5-di-tert-butyl-4-hydroxyphenyl) carbamate.
  • Esters of ⁇ - (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid with mono- or polyhydric alcohols for example with methanol, ethanol, n-octanol, isooctanol, octadecanol, 1,6-
  • Trimethylhexanediol trimethylolpropane, 4-hydroxymethyl-1-phosphate-2,6,7-trioxabicyclo [2,2,2] octane.
  • Esters of ⁇ - (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid with mono- or polyhydric alcohols for example with methanol, ethanol, n-octanol, isooctanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol , Trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] oct
  • Esters of ⁇ - (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid with monohydric or polyhydric alcohols for example with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1, 2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N 5 N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl- phospha-2, 6, 7-trioxabicyclo [2.2.2] octane.
  • Esters of 3,5-di-tert-butyl-4-hydroxy-phenylacetic acid with mono- or polyhydric alcohols for example with methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2 Propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N'-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, 4-hydroxymethyl- phospha-2, 6, 7-trioxabicyclo [2.2.2] octane.
  • Amides of ⁇ - (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid for example N, N'-bis- (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) hexamethylenediamide, N, N Bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) trimethylenediamide, N, N'-bis (3,5-di-tert-butyl (4-hydroxyphenylpropionyl) hydrazide, N.N ' bis [2- [3- [3,5-di-tert-butyl-hydroxyphenyl] propionyl oxy) ethyl oxamide (Naugard® XL-I sold by Uniroyal).
  • vitamin C Ascorbic acid (vitamin C).
  • Amine-type antioxidants for example N, N'-diisopropyl-p-phenylenediamine, N, N'-di-sec-butyl-p-phenylenediamine, N, N'-bis (l, 4-dimethylpentyl) -p-phenylenediarnine, N , N'-Bis- (1-ethyl-3-methylpentyl) -p-phenylenediamine, N, N'-bis (1-methylheptyl) -p-phenylenediamine, N, N'-dicyclohexyl-p-phenylenediamine, N, N '-Diphenyl-p-phenylenediamine, N, N'-bis (2-naphthyl) -p-phenylenediamine, N-isopropyl-N'-phenyl-p-phenylenediamine, N- (1,3-dimethylbutyl) -N
  • UV absorbers and light stabilizers such as
  • 2-hydroxybenzophenones for example the 4-hydroxy, 4-methoxy, 4-octyloxy, A-decyloxy, 4-dodecyloxy, 4-benzyloxy, 4,2 ', 4'-trihydroxy and 2' -Hydroxy-4,4'-dimethoxy derivatives.
  • Esters of substituted and unsubstituted benzoic acids such as 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis (4-tert-butylphenyl) butylbenzoyl) resorcinol, benzoylresorcinol, 2,4-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl-3, 5-di-tert-butyl-4-hydroxybenzoate, 2-methyl-4,6-di-tert-butylphenyl-3,5-di-tert-butyl-4-hydroxybenzoate.
  • Acrylates for example ethyl- ⁇ -cyano- ⁇ , ⁇ -diphenylacrylate, isooctyl- ⁇ -cyano- ⁇ , ⁇ -di-phenylacrylate, methyl- ⁇ -carbomethoxycinnamate, methyl- ⁇ -cyano- ⁇ -methyl-p-methoxy- cinnamate, butyl- ⁇ -cyano- ⁇ -methyl-p-methoxycinnamate, methyl- ⁇ -carbomethoxy-p-methoxycinnamate and N- ( ⁇ -carbomethoxy- ⁇ -cyanovinyl) -2-methylindoline.
  • Nickel compounds for example nickel complexes of 2,2'-thio-bis- [4- (1, 1,3,3-tetramethylbutyl) phenol], such as the 1: 1 or 1: 2 complex, with or without additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel ldibutyldithiocarbamate, nickel salts of the monoalkyl esters, for example the methyl or ethyl ester, of 4-hydroxy-3,5-di-tert-butylbenzylphosphonic acid, nickel complexes of ketoximes, for example of 2-hydroxy-4-methylphenyl undecyl ketoxime, nickel complexes of 1-phenyl-4-lauroyl-5-hydroxypyrazole, with or without additional ligands.
  • additional ligands such as n-butylamine, triethanolamine or N-cyclohexyldiethanolamine, nickel ldibutyldi
  • Sterically hindered amines for example bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (2,2,6,6-tetramethyl-4-piperidyl) succinate, bis (1,2,2, 6,6-pentamethyl-4-piperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1, 2,2,6,6-pentamethyl-4-) piperidyl) -n-butyl-3,5-di-tert-butyl-4-hydroxybenzyl malonate, the condensate of 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl-4-hydroxypiperidine and succinic acid, linear or cyclic condensates of N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-tert-octylamino-2,6-dich
  • Oxamides for example 4,4'-dioctyloxyoxanilide, 2,2'-diethoxyoxanilide, 2,2'-dioctyloxy-5,5'-di-tert-butoxanilide, 2,2'-didodecyloxy-5,5'-di- tert-butoxanilide, 2-ethoxy-2'-ethyl-oxanilide, N, N'-bis (3-dimethylaminopropyl) oxamide, 2-ethoxy-5-tert-butyl-2'-ethoxanilide and its mixture with 2-ethoxy- 2'-ethyl-5,4'-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides and mixtures of o- and P-ethoxy-di-substituted oxanilides.
  • Metal deactivators for example N, N'-diphenyloxamide, N-salicylal-N'-salicyloylhydrazine, N, N'-bis (saliceloyl) hydrazine, N, N'-bis (3,5-di-tert-butyl-4-) hydroxyphenylpropionyl) hydrazine, 3-salicyloylamino-1, 2,4-triazole, bis (benzylidene) oxalyldihydrazide, oxanilide, isophthaloyldihydrazide, sebacoylbisphenylhydrazide, N 5 N'-diacetyladipoyldihydrazide, N, N'-bis (salicyloyl) oxalyldihydrazide, N, N'-bis (salicyl oiyl) thiopropionyl dihydrazide.
  • Phosphites and phosphonites for example triphenyl phosphite, diphenyl alkyl phosphites, phenyl dialkyl phosphites, tris (nonylphenyl) phosphite, trilauryl phosphite, trioctadecyl phosphite, distearyl pentaerythritol diphosphite, tris (2,4-di-tert-butylphenyl) phosphite, diisodecylpentaerythritol diphosphite, bis (2,4-di-tert-butylphenyl) phosphite tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite,
  • Diisodecyloxypentaerythritol diphosphite bis (2,4-di-tert-butyl-6-methylphenyl) pentaerythritol diphosphite, bis (2,4,6-tris (tert-butylphenyl) pentaerythritol diphosphite, tristearylsorbitol triphosphite, tetrakis (2,4-di-tert-butylphenyl) tert-butylphenyl) -4,4'-biphenylene-di-phosphonite, 6-iso-octyl-oxy-2,4,8,10-tetra-tert-butyl-12H-dibenzo [d, g] -l, 3.2 dioxaphosphocine, 6-fluoro-2,4,8,10-tetra-tert-butyl-12-methyldibenzo [d, g] -l, 3,2-dioxa
  • phosphites tris (2,4-di-tert-butylphenyl) phosphite (Irgafos® 168, Ciba-Geigy), tris (nonylphenyl) phosphite.
  • Hydroxylamines for example N, N-dibenzylhydroxylamine, N, N-diethylhydroxylamine, N, N-dioetylhydroxylamine, N, N-dilaurylhydroxylamine, N, N-ditetradecylhydraxylamine, N, N-dihexadecylhydroxylamine, N, N-dioctadecylhydroxylamine, N-hexadecyl N-octadecylhydroxylamine, N-heptadecyl-N-octadecylhydroxylamine, N, N-dialkylhydroxylamine derived from hydrogenated tallow amine.
  • Nitrone for example N-benzyl- ⁇ -phenylnitrone, N-ethyl- ⁇ -methylnitrone, N-octyl- ⁇ -heptylnitrone, N-lauryl- ⁇ -undecyl-nitron, N-tetradecyl- ⁇ -tridecyl-nitron, N- Hexadecyl- ⁇ -pentadecylnitrone, N-octadecyl- ⁇ -heptadecylnitrone, N-hexadecyl- ⁇ -heptadecylnitrone, N-octadecyl- ⁇ -pentadecylnitrone, N-heptadecyl- ⁇ -heptadecylnitrone, N-octadecyl-o-hexadecyl nitrone, nitrone, derived from N, N-dialkylhydroxylamine derived from hydrogenated
  • Thio synergists for example dilauryl thiodipropionate or distearyl thiodipropionate.
  • Peroxide scavengers for example, esters of ⁇ -thiodipropionic acid, for example the
  • Polyamide stabilizers for example copper salts in combination with iodides and / or phosphorus compounds and salts of divalent manganese.
  • Basic costabilizers for example melamine, polyvinyl pyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, Polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate and potassium palmitate, antimony catecholate or tin catechinate.
  • Basic costabilizers for example melamine, polyvinyl pyrrolidone, dicyandiamide, triallyl cyanurate, urea derivatives, hydrazine derivatives, amines, Polyamides, polyurethanes, alkali metal salts and alkaline earth metal salts of higher fatty acids, for example calcium stearate, zinc stearate, magnesium behenate, magnesium stearate, sodium ricinoleate
  • Nucleating agents for example, inorganic substances such as talc, metal oxides such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of preferably alkaline earth metals; organic compounds such as mono- or polycarboxylic acids and the salts thereof, for example 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate; Polymer compounds, such as ionic copolymers (ionomers).
  • inorganic substances such as talc, metal oxides such as titanium dioxide or magnesium oxide, phosphates, carbonates or sulfates of preferably alkaline earth metals
  • organic compounds such as mono- or polycarboxylic acids and the salts thereof, for example 4-tert-butylbenzoic acid, adipic acid, diphenylacetic acid, sodium succinate or sodium benzoate
  • Polymer compounds such as ionic copolymers (ionomers).
  • Fillers and reinforcing agents for example calcium carbonate, silicates, glass fibers, glass bubbles, asbestos, talc, kaolin, mica, barium sulfate, metal oxides and hydroxides, carbon black, graphite, wood flour and flours or fibers of other natural products, synthetic fibers.
  • additives for example, plasticizers, lubricants, emulsifiers, pigments, rheology additives, catalysts, flow control agents, optical brighteners, antistatics, blowing agents and drip inhibitors.
  • Benzofuranones and indolinones for example those disclosed in U.S. Pat. Nos. 4,325,863; 4, 338, 244; 5,175,312; 5,216,052; 5,252,643; DE-A 43 16 611; DE-A 43 16 622; DE-A 43 16 876; EP-A 0 589 839 or EP-A 0 591 102 or 3- [4- (2-acetoxyethoxy) -phenyl] -5,7-di-tert-butylbenzofuran-2-one, 5,7-di-tert-butylbenzofuran-2-one butyl 3- [4- (2-stearoyloxyethoxy) phenyl] benzofuran-2-one, 3,3'-bis [5,7-di-tert-butyl-3- (4- [2-hydroxyethoxy] phenyl) benzofuran-2-one], 5,7-di-tert-butyl-3- (4-ethoxy
  • Suitable lubricants are, for example: montan wax, fatty acid esters, PE waxes, amide waxes, polyol partial esters, partially saponified PE waxes, so-called complex ester chloroparaffins, glycerol esters, alkaline earth metal soaps or fatty ketones, as described in DE 42 04 887. Suitable lubricants are also described in "Taschenbuch der Kunststoffadditive", editors R. Gachter and H. Muller, Hanser Verlag, 3rd edition, 1990, pages 443-503 Combinations of lubricants are found in EP 0 062 813 and EP 0 336 289.
  • the present composition may additionally contain other UV absorbers selected from the group consisting of the s-triazines, the oxanilides, the hydroxybenzophenones, benzoates and the ⁇ -cyanoacrylates.
  • the present composition may additionally contain an effective stabilizing amount of at least one further 2-hydroxyphenyl-2H-benzotriazole, another trisaryl-s-triazine or hindered amine or mixtures thereof.
  • additional components are selected from pigments, dyes, plasticizers, antioxidants, thixotropic agents, leveling agents, basic co-stabilizers, other light stabilizers such as UV absorbers and / or hindered amines, metal passivators, metal oxides, organophosphorus compounds, hydroxylamines, and mixtures thereof.
  • pigments phenolic antioxidants, calcium stearate, zinc stearate, phosphite and phosphonite stabilizers, benzofuran stabilizers, UV absorbers of the 2- (2'-hydroxyphenyl) benzotriazole and 2- (2-hydroxyphenyl) -1,3,5-triazine classes and sterically hindered amines.
  • the present invention further relates to the use of the flame retardant composition of the invention for the flame retardant finishing of polymers or polymer blends.
  • the polymer or polymer substrate may be any of a wide variety of polymer types including polyolefins, polyesters, polyamides, ABS polymers.
  • the polymers are particularly preferably polypropylene, polyethylene, thermoplastic olefin (TPO), ABS and impact-resistant polystyrene; Particularly preferred are polypropylene, polyethylene and thermoplastic olefin (TPO), thermoplastic polyurethane elastomers (TPU), polyvinyl chloride (PVC), polyvinyl acetate (PVA), ethyl vinyl acetate (EVA), polyester resins (UP resins), polyureas and polyurethanes.
  • TPO thermoplastic olefin
  • TPU thermoplastic polyurethane elastomers
  • PVC polyvinyl chloride
  • PVA polyvinyl acetate
  • EVA ethyl vinyl acetate
  • UP resins polyester resins
  • the effective flame retardant amount of the flame retardant composition of the present invention is that needed to exhibit flame retardancy is measured by one of the standard methods used to evaluate flame retardancy. These include the NFPA 701 Standard Fire Test Procedures for Flame Retardant Fabrics and Films 1989 and 1996 Edition; Electro UL 94 Flammability Test of Plastic Materials for Parts in Devices and Equipment, 5th Edition, October 29, 1996, Limiting Oxygen Index (LOI), ASTM-D2863 and Cohen Calorimetry ASTM E-1354. Furthermore, the standards for buildings (DIN4102B1) and for motor vehicles (MVSS 302) for examining the flame retardant properties of the flame retardant composition of the invention.
  • DIN4102B1 Standard Fire Test Procedures for Flame Retardant Fabrics and Films 1989 and 1996 Edition
  • Electro UL 94 Flammability Test of Plastic Materials for Parts in Devices and Equipment 5th Edition, October 29, 1996
  • LOI Limiting Oxygen Index
  • ASTM-D2863 ASTM-D2863
  • the present invention thus also relates to a flame retardant composition
  • a flame retardant composition comprising:
  • the effective flame retardant amount of the flame retardant composition of the invention is suitably 0.1 to 60% by weight, preferably 0.5 to 30% by weight, more preferably 1 to 10% by weight, based on the polymer.
  • the flame retardant polymers containing the flame retardant compositions of the present invention may be prepared by known methods, for example, by blending the noted additives and optionally other additives with the polymer using equipment such as calenders, mixers, kneaders, extruders, and the like.
  • the additives can be added individually or in admixtures with each other. It is also possible to use so-called masterbatches.
  • the polymer can be used in the form of powders, granules, solutions, suspensions or in the form of latexes.
  • the flame retardant polymer compositions thus obtained can be formed into the desired shape by known methods.
  • Such processes include, for example, calendering, extruding, injection molding, spray coating, knife coating, spinning, compression melting, rotational molding, thermoforming or extrusion blow molding.
  • the finished flame-retardant polymer can also be made into foamed articles.
  • the polymer articles produced therewith are, for example, fibers, films, molded articles and foamed articles.
  • the additives according to the invention and optionally other components can be added to the polymer material individually or mixed with each other. If desired, the individual components may be mixed together prior to incorporation into the polymer, for example by dry blending, densification or in the melt.
  • the invention relates to a process for imparting flame retardant properties to a polymer, which process comprises adding components (A) (one or more diphosphonate compound (s)) and (B) (one or more 1,3,5 Triazine compound (s)) to the polymer.
  • the effective flame retardant amount of components (A) and (B) is that needed to detect flame retardant effectiveness, as can be measured by one of the standard methods described above.
  • room temperature means a temperature in the range of 20 to 25 ° C. Percentages are by weight of the polymer substrate, unless otherwise specified.
  • polyethylene films are prepared which have been mixed with different flame retardant compositions:
  • the films are produced on a Einschneckenextruder 19 / 25D Fa. Brabender at a melt temperature of 210 0 C and a speed at which a maximum of 50% of the torque can be achieved.
  • the powder mixtures according to Examples 1 to 23 are thereby fed manually via a funnel.
  • the tool is a broad-band nozzle head 100 x 0.5 mm, the discharge belt is adjusted so that a film width of 90 mm and a thickness of 0.20 mm are achieved. The cooling takes place in the air.
  • test specimens measuring 230 mm x 90 mm are produced. These are then clamped vertically in a combustion chamber. The flame is made on the surface with a flame height of 20 mm and a flame angle of 45 °.
  • This DIN corresponds to DIN 4102-B2, provided that the upper measuring mark of the combustion body is not reached by the flame tip or extinguishes by itself.
  • Domus HM 41 TM melamine hydrobromide
  • TM poly- [2,4- (piperazin-l, 4-yl) -6- (morpholin-4-yl] -l, 3,5triazine.
  • the amount of flame retardant based on the finished polymer compound, which is necessary to achieve the LOI of the individual substance, can be significantly reduced by using the synergistic flame retardant composition.
  • the synergistic composition can thus also, due to the lower proportion of flame retardants, thin-walled molding materials or nonwovens produce that meet the required fire class.

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Abstract

L'invention concerne une composition retardatrice de flamme renfermant un mélange d'agent retardateur de flamme synergique, ainsi qu'un procédé destiné au retardement de flamme d'un polymère par addition de la composition retardatrice de flamme. L'invention concerne en outre des polymères renfermant ladite composition retardatrice de flamme.
PCT/EP2009/061489 2008-09-05 2009-09-04 Composition retardatrice de flamme renfermant un dérivé de l'acide phosphonique WO2010026230A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
DK09782635.8T DK2331625T3 (da) 2008-09-05 2009-09-04 Flammebeskyttelsespræparat indeholdende et phosphonsyrederivat
AT09782635T ATE541889T1 (de) 2008-09-05 2009-09-04 Flammschutzzusammensetzung enthaltend ein phosphonsäurederivat
US12/737,924 US8349925B2 (en) 2008-09-05 2009-09-04 Flame-retardant composition comprising a phosphonic acid derivative
EP09782635A EP2331625B1 (fr) 2008-09-05 2009-09-04 Composition retardatrice de flamme renfermant un dérivé de l'acide phosphonique
US13/705,058 US8853307B2 (en) 2008-09-05 2012-12-04 Flame-retardant composition comprising a phosphonic acid derivative

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP08163790.2 2008-09-05
EP08163790 2008-09-05

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/737,924 A-371-Of-International US8349925B2 (en) 2008-09-05 2009-09-04 Flame-retardant composition comprising a phosphonic acid derivative
US13/705,058 Division US8853307B2 (en) 2008-09-05 2012-12-04 Flame-retardant composition comprising a phosphonic acid derivative

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EP2666626A1 (fr) 2012-05-23 2013-11-27 Sekisui Alveo AG Mousse de polyoléfine ignifuge et sa production
DE102013012487A1 (de) 2013-07-26 2015-01-29 Clariant International Ltd. Zusammensetzung aus einem thermoplastischen Polymer und einer synergistischen Mischung aus bestimmten Aminoethern und feinteiligen Phosphinaten
EP2927302A1 (fr) 2014-04-03 2015-10-07 Basf Se Moyen de protection contre les flammes à base de liaisons de di-, tri- et tétra-aryléthane substituées
EP2947115A1 (fr) 2014-05-22 2015-11-25 Basf Se Mélanges ignifuges sans halogène pour polyoléfine en mousse
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US10214631B2 (en) 2012-11-19 2019-02-26 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Polymer composition with improved long-term stability, moulded parts produced herefrom and also purposes of use
WO2019092163A1 (fr) 2017-11-13 2019-05-16 Clariant Plastics & Coatings Ltd Nouvelles compositions ignifuges pour polyoléfines
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JP2020097716A (ja) * 2018-12-18 2020-06-25 株式会社フジクラ 難燃性樹脂組成物、ケーブル用難燃性樹脂組成物、これを用いたケーブル、成形体及び難燃剤マスターバッチ並びに難燃剤
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WO2011101274A1 (fr) * 2010-02-22 2011-08-25 Ika Innovative Kunststoffaufbereitung Gmbh & Co. Kg Système stabilisateur pour polymères halogénés expansibles
EP2666626A1 (fr) 2012-05-23 2013-11-27 Sekisui Alveo AG Mousse de polyoléfine ignifuge et sa production
WO2013174482A1 (fr) 2012-05-23 2013-11-28 Sekisui Alveo Ag Mousse de polyoléfine ignifuge et production de celle-ci
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US10913743B2 (en) 2013-03-25 2021-02-09 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Use of organic oxyimides as flame retardant for plastic materials and also flame-retardant plastic material composition and moulded parts produced therefrom
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EP2927302A1 (fr) 2014-04-03 2015-10-07 Basf Se Moyen de protection contre les flammes à base de liaisons de di-, tri- et tétra-aryléthane substituées
EP2947115A1 (fr) 2014-05-22 2015-11-25 Basf Se Mélanges ignifuges sans halogène pour polyoléfine en mousse
US10370537B2 (en) 2014-05-28 2019-08-06 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Use of oxyimide-comprising copolymers or polymers as flame retardants, stabilisers, rheology modifiers for plastic materials, initiators for polymerisation- and grafting processes, crosslinking- or coupling agents and also plastic moulding compounds comprising such copolymers or polymers
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CN107148441B (zh) * 2014-10-03 2020-11-27 钟化比利时公司 聚烯烃系树脂预发泡粒子和模内发泡成型体以及它们的制造方法
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WO2018137883A2 (fr) 2017-01-24 2018-08-02 Thor Gmbh Composition ignifuge à effet amélioré renfermant un dérivé d'acide phosphonique
WO2019092163A1 (fr) 2017-11-13 2019-05-16 Clariant Plastics & Coatings Ltd Nouvelles compositions ignifuges pour polyoléfines
WO2020215700A1 (fr) * 2019-04-23 2020-10-29 台州市黄岩广环工贸有限公司 Matériau de polypropylène ignifuge sans halogène pour parties de contact électrique de véhicules électriques conformément à gb17761-2018 et son procédé de moulage par injection
WO2021170599A1 (fr) * 2020-02-27 2021-09-02 Basf Se Compositions de polyoléfine
EP4365225A1 (fr) 2022-11-04 2024-05-08 Clariant International Ltd Composition ignifuge, composition polymère la comprenant et son utilisation
WO2024094455A1 (fr) 2022-11-04 2024-05-10 Clariant International Ltd Composition ignifuge, composition polymère la comprenant et son utilisation

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US20140005289A1 (en) 2014-01-02
EP2450401B1 (fr) 2013-04-17
EP2331625B1 (fr) 2012-01-18
US20110257310A1 (en) 2011-10-20
US8853307B2 (en) 2014-10-07
EP2331625A1 (fr) 2011-06-15
ATE541889T1 (de) 2012-02-15

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